


You Gotta Learn Somehow

by Corbella0417



Category: Supernatural
Genre: Anal Fingering, Anal Sex, First Time, M/M, Wincest - Freeform, dean is an understanding brother, not really sure where this came from but go with it, underage!Sam
Language: English
Status: Completed
Published: 2015-01-27
Updated: 2015-01-27
Packaged: 2018-03-09 08:34:57
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3243179
Author URL: https://archiveofourown.org/users/Corbella0417/pseuds/Corbella0417
Summary: <blockquote class="userstuff">
              <p>When Dean walks in on his brother Sam is embarrassed. Dean is hesitant at first but he helps him out.</p>
            </blockquote>





	You Gotta Learn Somehow

**Author's Note:**

> In this Sam is underage because he's sixteen in this fic. Don't hate... 
> 
> I have no Beta so any mistakes are my own.

Dean woke up to the sounds of moaning and grunting coming from the bathroom. He looked to check on Sam but found his bed to be empty. Filling with worry he got up and snuck to the bathroom door, pushing it open just enough to peak inside. 

Dean froze when he saw Sam, face red with his foot on the toilet seat as he tried to work a small dildo into himself. He didn’t know what to do. Should he say something? Or should he just go back to bed and forget what he saw? 

Before he could make a move Sam turned his head and yelped, quickly falling back and into the tub with a thump. 

“What the hell Dean!?” Sam shouted as he scramble to get up and cover himself. 

“S-sorry…” Dean mumbled as he shut the door and backed away. 

He walked to the bed and sat down hard as he tried to wrap his mind around what he just saw. And how it made him feel. 

Sam came out fully dressed a few minutes later, his face bright red in embarrassment. He walked up and stepped in front of Dean, his eyes on the floor. 

“I’m sorry,” they said in unison. 

Dean looked up at his brother in confusion. “What are you sorry for? I’m the one who was watching you.” 

Sam glanced at him but looked back down quickly. “I just wanted to try it. I mean…I know you’ve done it…and I just…” 

Dean chuckled at him. “You know I’ve done it so you wanted to as well,” he said for him. Sam nodded, his face going even redder now. 

Sam felt like an idiot and he was afraid Dean did too. “Please don’t tell anyone…” Dean felt a stab at that, sad that Sam would think he would do that. 

“Hey,” he said as he made his little brother look at him. “You know me Sam. You know I would never tell anyone.” 

Sam nodded. “I know, I just… God I’m so embarrassed!” He moved away and flopped onto his bed, his face hidden in the pillow. Dean felt bad for him and moved to the other bed to join him. 

He debated asking but decided to go for it. “Well did you…like it?” He asked hesitantly. 

“I- - wa- - un- -” Sam said, his voice muffled badly. 

“What?” Dean asked as he leaned closer. 

Sam rolled over so he could look at Dean. “I said it was uncomfortable. It burned and I couldn’t make it feel good.” 

Dean laughed. “Well the first time is always hard, especially doing it alone. Did you use enough lube?” The look on Sam’s face was answer enough. “Did you use any at all?” Sam shook his head and felt even dumber. How could he not know to use lube? 

“Hey it’s fine, don’t worry about it!” Dean said as he gave him a playful shove. “You just need someone who can teach you that’s all.” He moved to get off the bed when he felt a hand on his leg. 

“Can you teach me?” Sam asked shyly. 

Dean froze and looked at him with wide eyes. “Sam I- -” 

Sam sat up and gave him those big puppy eyes. “Please Dean… You know how. I promise I’ll never say a word! I just…I trust you.” 

Dean felt conflicted. Sam was his brother, his little brother. But he also couldn’t ignore how he felt when he saw him like that. How hard he got listening to him moan. “Sam…” He looked at his brother and pushed his thoughts away. Sam wanted to learn, and as his brother it was his job to teach him. If he didn’t and Sam went somewhere else he could get hurt. At least this way he knew Sam would be safe. “Ok fine, I’ll teach you. Go ahead and strip, I’ll be right there.” 

As Sam started undressing Dean searched through his bag, pulling out the lube and a condom. When he turned around Sam was waiting for him by the bed. “Climb up,” Dean said as he motioned to the bed. 

Sam did as he was told, leaning back as he watched Dean strip. Dean climbed up next to him and pushed him back, settling himself between Sam’s legs. He slicked up his fingers and pressed one against his entrance. Sam immediately tensed up, clenching hard at the strange feeling. 

“Relax Sam…I’ve got you.” He waited until Sam was relaxed enough, slipping the tip of his finger in easily. 

The burn of the stretch was really uncomfortable for Sam. His hips bucked as he bit his lip, trying to keep his noises down. But Dean was gentle with him, going slow enough that soon the burn turned to pleasure and his hips bucked for more. When he had up to three Sam was already moaning, his pupils blown as he looked at his older brother. “Dean please, I’m ready, please!” 

The older boy took a moment before pulling his fingers out and ripping the foil packet open. After sliding on the condom he paused, wondering if he could actually do this. But then Sam whimpered, rolling his hips as he reached out for him. 

Dean took a breath and pushed in, moving at an agonizingly slow pace so as not to hurt him. Sam exhaled at the full feeling and winced at the stretch. Dean was pretty big and his hole felt like it could split any second. But then the stretch turned to pleasure and he started bucking, pressing his aching cock against Dean’s stomach in search of release. 

When Dean knew he was ready he started to move, pulling back out before carefully sliding back in. Sam’s back arched at the pleasure as Dean’s cock found that sensitive bundle of nerves, sending shock waves through his body. He couldn’t control his noises now as Dean rocked into him, pressing them closer with each thrust. 

Then he felt it, that heat low in his gut. “Dean…ah! I’m close!” 

Dean sped up his movements as he got closer as well. “Touch yourself Sam,” he growled out as he slammed into him. Sam obeyed, stroking himself quickly as his orgasm neared. 

Sam came hard, shooting onto his stomach and hand with a loud cry. Dean came right after as Sam clenched around him tight, milking him dry. 

Dean hovered over him for a minute before pulling out, tossing the condom into the trash can before laying on his back. Sam followed and laid next to him, panting hard but with a big smile on his face. “That was…great!” Sam said with tired excitement.

Dean smiled and laughed, glad to know that his first time was good for him. When Sam rolled over and kissed him Dean was stunned but melted quickly into the kiss. Sam curled up next to him and fell asleep quickly. 

Dean laid there for awhile and tried to go through what just happened. He should be freaking out, he just slept with his brother. But looking at Sam as he slept there peacefully made him relax a little. At least Sam was safe with him. That’s all that mattered.


End file.
